by Dan Millott
When Ted Smallwood arrived on Chokoloskee Island in 1897, he joined five other pioneering families there. He soon saw the need for a place where the settlers could get supplies and trade products they grew or hunted. So the idea for Ted Smallwood’s Store was hatched. Beginning in 1906, the trading post first operated out of Smallwood’s house; the store was eventually built in 1917 at its current location on the shores of Chokoloskee Bay.
Chokoloskee and nearby Everglades City developed as an outpost for white settlers in the inhospitable Everglades and, for a while, served as the center of civilization in Collier County. Naples has long since usurped that title, but a trip to this part of the Ten Thousand Islands reveals distinct traces of its former character and sheds light on the role these communities played in Southwest Florida’s history.
In Smallwood’s time, for example, the pioneers of Southwest Florida did not have the advantage of hurricane-hunter planes or technology for long-range weather forecasts. So if a hurricane came, it was with little warning. Lynn McMillin, Smallwood’s granddaughter and the driving force behind the restoration of Ted Smallwood’s Store to its early twentieth-century condition, says some early brushes with Mother Nature prompted Smallwood to elevate his store on pilings to protect it from hurricane flood tides.
“Rising water destroyed merchandise in a couple of storms when the store was still at ground level,” she says. “But a major killer hurricane on the East Coast prompted my grandfather to elevate the store with railroad pilings.” That work was completed in 1925.
Hurricane Donna slammed Chokoloskee and nearby Everglades City in September of 1960. Most parts of the island were flooded, but the store withstood the storm.
Ted Smallwood’s Store was listed on the National Register of Historic Places in 1974 and continued to operate until 1982, about thirty years after Smallwood died. It closed after McMillin’s aunt, who later had owned the store, also passed away. At that point, McMillin, a lifelong resident of Chokoloskee, saw a need to preserve the store because of the history it holds. She persuaded her aunt’s five brothers and sisters to sell their interests to her.
But the years, wind, and salt air had not been kind to the old structure. “We had to replace the windows, repair the roof, and replace the dock at the water’s edge,” McMillin says. Money had to be raised to get the old store up and running.
During the store’s early years, Seminole Indians living near Chokoloskee Island were among Smallwood’s customers. Their descendants recognized the store as a part of their history too, and the first offer of a major cash contribution for the restoration came from Chief James Billie of the Seminole Tribe.
That seed money enabled McMillin and other supporters of the restoration, including the late author Marjory Stoneman Douglas, to successfully seek matching funds from the State of Florida. The first major grant in 1990 went toward the restoration, and additional grants were secured to complete the job.
By 1991, the store had reopened as a museum, two years after the restoration began. Visitors today find merchandise much as it appeared to patrons in 1917. Historic Smallwood Store also operates a gift shop and sells numerous written histories of the area.
As a small museum, it competes for state funds with operations of similar size. It also raises money through benefits, such as an annual Seminole Festival in late March and a re-enactment by a Chokoloskee theater troupe of the murder of Edgar Watson. The vigilante was killed at Ted Smallwood’s Store in 1910, a story made famous by Peter Matthiessen’s book Killing Mr. Watson.
A Company Town Before the Tamiami Trail was completed in the mid-1920s, sea-lanes were the region’s only means of commerce, and Chokoloskee Island was a main stopping point for boat traffic between Key West and Tampa. Even Naples residents went by boat to trade at Ted Smallwood’s Store before there were highways. Chokoloskee Island itself was not connected to the mainland by a road until the mid-1950s.
Although Chokoloskee and Everglades City today boast relatively small populations, at one time they were the centers of power in Collier County. Everglades City was the county seat and was home to the county courthouse; the Bank of Everglades, which was the only bank in the county until the early 1950s; Collier Corporation, operator of Barron Collier’s vast holdings; and the Collier County News, before it moved to Naples.
Barron Collier, for whom the county is named, left his mark throughout the area. He had made his fortune in New York City, providing advertising on buses and subway cars. His holdings included more than two thousand square miles of land in Lee County. He offered the state free right-of-way for the planned Tamiami Trail if a new county were formed and named for him, which the state did in 1923.
If ever there was a company town, Everglades City was it. The houses were owned by Collier and rented by the residents. The bank was his, as was the newspaper and the Intercounty Telephone Company that eventually served much of Southwest Florida until the 1960s.
The early days of Everglades City were high times for the town, but several years later, high water would do it in. By the late 1950s, Everglades City, once the population center of the county, had lost that distinction to Naples. A petition drive by the Naples Junior Chamber of Commerce put a proposition on the ballot in 1959, seeking to move the courthouse from Everglades City. Voters selected East Naples as the site for the new county seat, and the county set up shop in its new East Naples courthouse in 1962.
But there were more blows to come for Everglades City. Early on the morning of September 10, 1960, Hurricane Donna vanquished the community with a tidal surge eight feet high in the middle of town. Seawater was measured a foot high on the first floor of the courthouse. The Manhattan Mercantile store, immediately across the street from the courthouse, had a watermark near the ceiling of the store marking Donna’s visit.
And the bad news came in threes. After the hurricane and the vote to move the courthouse, the Collier Corporation relocated to Naples too.
Natural Appeal Everglades City was experiencing some other changes as well, and they weren’t all detrimental. The area became the western gateway to Everglades National Park in 1953, which has benefited the area by luring visitors.
Because roadways came comparatively late to Everglades City and Chokoloskee, most people arrived by water or rail. Everglades City’s railroad station stopped seeing Atlantic Coast Line trains in 1956, but until then, trains brought passengers to the city, who made their way to the nearby Rod and Gun Club.
Opened in the early 1890s, the Rod and Gun Club was purchased by Barron Collier in 1923 and was a popular destination for fishermen, sportsmen, and the politically powerful. President Harry Truman lunched there after the federal government secured land for Everglades National Park, and General Dwight D. Eisenhower visited before he became president.
To illustrate the preferred mode of transportation, the “front” of the Rod and Gun Club faces the Barron River, where boats would dock, instead of the driveway, where cars would approach the building. The club still operates, offering accommodations and a dining room that serves lunch, along with dinner during the winter season.
The Atlantic Coast Line depot remained dormant for several years, but the building was expanded and refurbished in the 1970s and opened as the Captain’s Table Restaurant. It has since changed ownership and is now the Everglades Seafood Depot Restaurant.
Opportunities for Exploration Near Chokoloskee Causeway, Everglades National Park Boat Tours operates ninety-minute tours of the mangrove wilderness. The tours start near the ranger station, just south of Everglades City, on the road that leads to Chokoloskee Island. Canoe rentals also are available.
While in Everglades City, visitors can learn more about Collier County’s past at the Museum of the Everglades. The pink building was once a laundry and also served as the home of the Collier Corporation before its move to Naples. Permanent displays detail the history of the region, while rotating exhibits spotlight the work of local artists.
On U.S. 41 near Royal Palm Hammock, the 7,271-acre Collier-Seminole State Park is the site of the “Walking Dredge” used to clear the land and muck for construction of the Tamiami Trail. The park also has a monument to Barron Collier, who gave the land to the state in 1947. Campsites, nature trails, and a wealth of vegetation and wildlife typical of the Florida Everglades can all be found here, and boat tours are also available.
Just east of State Road 29 on U.S. 41 is the village of Ochopee, home of the nation’s smallest post office. The postmistress gladly hand-cancels postcards depicting the post office for visitors to prove they were there. And despite its diminutive size, the Ochopee Post Office serves nearly one thousand postal patrons, including residents of the Miccosukee Indian Reservation in western Miami-Dade County.
The stretch of U.S. 41 from State Road 951 east to State Road 29—the access highway to Everglades City and Chokoloskee—has been designated as a State Scenic Highway. So enjoy the scenery and the history on a trip into Southwest Florida’s colorful past.